UA67760C2 - Имидазонафтиридины и их применение для индуцирования биосинтеза цитокинов - Google Patents
Имидазонафтиридины и их применение для индуцирования биосинтеза цитокинов Download PDFInfo
- Publication number
- UA67760C2 UA67760C2 UA2000074070A UA00074070A UA67760C2 UA 67760 C2 UA67760 C2 UA 67760C2 UA 2000074070 A UA2000074070 A UA 2000074070A UA 00074070 A UA00074070 A UA 00074070A UA 67760 C2 UA67760 C2 UA 67760C2
- Authority
- UA
- Ukraine
- Prior art keywords
- aryl
- heteroaryl
- heterocyclyl
- oralalkyl
- group
- Prior art date
Links
- 102000004127 Cytokines Human genes 0.000 title claims abstract description 32
- 108090000695 Cytokines Proteins 0.000 title claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 24
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical class C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 301
- 238000000034 method Methods 0.000 claims abstract description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 241001465754 Metazoa Species 0.000 claims description 23
- -1 2-hydroxy-2-methylpropyl Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000036142 Viral infection Diseases 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 230000001939 inductive effect Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 abstract description 18
- 108010050904 Interferons Proteins 0.000 abstract description 18
- 229940079322 interferon Drugs 0.000 abstract description 18
- 239000000543 intermediate Substances 0.000 abstract description 18
- 238000002360 preparation method Methods 0.000 abstract description 10
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 7
- 102000003390 tumor necrosis factor Human genes 0.000 abstract description 7
- ZZXQWFQBPSUCAF-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-b][1,8]naphthyridine Chemical compound N1C2=NC=CC=C2C=C2C1NCN2 ZZXQWFQBPSUCAF-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000840 anti-viral effect Effects 0.000 abstract description 2
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 468
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
- 239000011541 reaction mixture Substances 0.000 description 144
- 239000007787 solid Substances 0.000 description 112
- 239000000243 solution Substances 0.000 description 110
- 238000006243 chemical reaction Methods 0.000 description 108
- 238000004458 analytical method Methods 0.000 description 93
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 91
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- 239000000203 mixture Substances 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 72
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 71
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 58
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 45
- 235000019341 magnesium sulphate Nutrition 0.000 description 45
- 239000000741 silica gel Substances 0.000 description 45
- 229910002027 silica gel Inorganic materials 0.000 description 45
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 239000000126 substance Substances 0.000 description 38
- 239000010410 layer Substances 0.000 description 37
- 238000001914 filtration Methods 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 31
- 239000003921 oil Substances 0.000 description 30
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- 239000000843 powder Substances 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 26
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 25
- 238000004809 thin layer chromatography Methods 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 23
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 22
- 230000003993 interaction Effects 0.000 description 22
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 22
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 238000009835 boiling Methods 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 19
- 229910003446 platinum oxide Inorganic materials 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 230000003197 catalytic effect Effects 0.000 description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000000908 ammonium hydroxide Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 239000012266 salt solution Substances 0.000 description 13
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 230000006698 induction Effects 0.000 description 10
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 230000003612 virological effect Effects 0.000 description 10
- 238000007796 conventional method Methods 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002027 dichloromethane extract Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 230000028993 immune response Effects 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 5
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 5
- 102100033891 Arylsulfatase I Human genes 0.000 description 5
- 101000925544 Homo sapiens Arylsulfatase I Proteins 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000120 cytopathologic effect Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical group CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- NQUIRWXTTAMWIU-UHFFFAOYSA-N 1h-1,8-naphthyridin-4-one Chemical compound C1=CC=C2C(O)=CC=NC2=N1 NQUIRWXTTAMWIU-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical class NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 description 3
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 3
- 241000710188 Encephalomyocarditis virus Species 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 210000005260 human cell Anatomy 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 3
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 2
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 2
- TZDMCKHDYUDRMB-UHFFFAOYSA-N 2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetic acid Chemical compound CC1=CN(CC(O)=O)C(=O)NC1=O TZDMCKHDYUDRMB-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- BIGVMITVYSKPHR-UHFFFAOYSA-N 3-(5-methyltetrazol-1-yl)pyridine-4-carboxylic acid Chemical compound CC1=NN=NN1C1=CN=CC=C1C(O)=O BIGVMITVYSKPHR-UHFFFAOYSA-N 0.000 description 2
- FYEQKMAVRYRMBL-UHFFFAOYSA-N 3-aminopyridine-4-carboxylic acid Chemical compound NC1=CN=CC=C1C(O)=O FYEQKMAVRYRMBL-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 241000701022 Cytomegalovirus Species 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000011953 bioanalysis Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- GJWSUKYXUMVMGX-UHFFFAOYSA-N citronellic acid Chemical compound OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- TWSXTXIKUVDTET-UHFFFAOYSA-N ethyl 2-(5-methyltetrazol-1-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1N1C(C)=NN=N1 TWSXTXIKUVDTET-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 2
- 201000005296 lung carcinoma Diseases 0.000 description 2
- 206010025135 lupus erythematosus Diseases 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- ZNBIZPXNJOMSFQ-UHFFFAOYSA-N methyl 4-[hydroxy(phenyl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(O)C1=CC=CC=C1 ZNBIZPXNJOMSFQ-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- IVKNUIVDQMARCO-UHFFFAOYSA-N oxazin-4-one Chemical compound O=C1C=CON=C1 IVKNUIVDQMARCO-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 2
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 201000010153 skin papilloma Diseases 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 230000029812 viral genome replication Effects 0.000 description 2
- PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
- AQOSPGCCTHGZFL-UHFFFAOYSA-N 1-(3a-hydroxy-7-methoxy-1,2,4,8b-tetrahydropyrrolo[2,3-b]indol-3-yl)ethanone Chemical compound COC1=CC=C2NC3(O)N(C(C)=O)CCC3C2=C1 AQOSPGCCTHGZFL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- QMJMEKNSAZDTIH-UHFFFAOYSA-N 2,2-diethoxyethyl acetate Chemical compound CCOC(OCC)COC(C)=O QMJMEKNSAZDTIH-UHFFFAOYSA-N 0.000 description 1
- RMFSFKGHOJGVIS-UHFFFAOYSA-N 2-(5-methyltetrazol-1-yl)pyridine-3-carboxylic acid Chemical compound CC1=NN=NN1C1=NC=CC=C1C(O)=O RMFSFKGHOJGVIS-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- HMBBEVMGBHTFAV-UHFFFAOYSA-N 2-methyl-1-[(3-nitro-1,5-naphthyridin-4-yl)amino]propan-2-ol Chemical compound C1=CN=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C=NC2=C1 HMBBEVMGBHTFAV-UHFFFAOYSA-N 0.000 description 1
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
- PGUPJAPHYIEKLT-UHFFFAOYSA-N 2-pyridin-4-ylsulfanylacetic acid Chemical compound OC(=O)CSC1=CC=NC=C1 PGUPJAPHYIEKLT-UHFFFAOYSA-N 0.000 description 1
- KCLKMYQLVMTDRL-UHFFFAOYSA-N 2-pyrimidin-2-ylethanethioic s-acid Chemical compound OC(=S)CC1=NC=CC=N1 KCLKMYQLVMTDRL-UHFFFAOYSA-N 0.000 description 1
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 description 1
- AIPCSKRJJOUNEM-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoyl chloride Chemical compound CC(C)(C)C1=CC(C(Cl)=O)=CC(C(C)(C)C)=C1O AIPCSKRJJOUNEM-UHFFFAOYSA-N 0.000 description 1
- LPUBRQWGZPPVBS-UHFFFAOYSA-N 3-butoxypropan-1-amine Chemical compound CCCCOCCCN LPUBRQWGZPPVBS-UHFFFAOYSA-N 0.000 description 1
- FVMDYYGIDFPZAX-UHFFFAOYSA-N 3-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=CC(O)=C1 FVMDYYGIDFPZAX-UHFFFAOYSA-N 0.000 description 1
- BPZZDZZOBAZEPJ-UHFFFAOYSA-N 3-nitro-1h-1,5-naphthyridin-4-one Chemical compound C1=CN=C2C(O)=C([N+]([O-])=O)C=NC2=C1 BPZZDZZOBAZEPJ-UHFFFAOYSA-N 0.000 description 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical group C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 description 1
- NARHAGIVSFTMIG-UHFFFAOYSA-N 4-(dimethylamino)-2,2-diphenylpentanamide Chemical compound C=1C=CC=CC=1C(C(N)=O)(CC(C)N(C)C)C1=CC=CC=C1 NARHAGIVSFTMIG-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 1
- FDOIXMGDTOEUQL-UHFFFAOYSA-N 4-chloro-3-nitro-1,5-naphthyridine Chemical compound C1=CC=NC2=C(Cl)C([N+](=O)[O-])=CN=C21 FDOIXMGDTOEUQL-UHFFFAOYSA-N 0.000 description 1
- ZGZLYKUHYXFIIO-UHFFFAOYSA-N 5-nitro-2h-tetrazole Chemical compound [O-][N+](=O)C=1N=NNN=1 ZGZLYKUHYXFIIO-UHFFFAOYSA-N 0.000 description 1
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 206010059313 Anogenital warts Diseases 0.000 description 1
- 101001074560 Arabidopsis thaliana Aquaporin PIP1-2 Proteins 0.000 description 1
- 201000002909 Aspergillosis Diseases 0.000 description 1
- 208000036641 Aspergillus infections Diseases 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000013165 Bowen disease Diseases 0.000 description 1
- 208000019337 Bowen disease of the skin Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100123850 Caenorhabditis elegans her-1 gene Proteins 0.000 description 1
- 101100153505 Caenorhabditis elegans tni-1 gene Proteins 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 229930008398 Citronellate Natural products 0.000 description 1
- 208000000907 Condylomata Acuminata Diseases 0.000 description 1
- 208000006081 Cryptococcal meningitis Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 101100163433 Drosophila melanogaster armi gene Proteins 0.000 description 1
- 101100010343 Drosophila melanogaster lobo gene Proteins 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 101000985278 Escherichia coli 5-carboxymethyl-2-hydroxymuconate Delta-isomerase Proteins 0.000 description 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 208000004554 Leishmaniasis Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 102100040448 Leukocyte cell-derived chemotaxin 1 Human genes 0.000 description 1
- 206010027209 Meningitis cryptococcal Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical group 0.000 description 1
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 1
- NDCGVLJXFQKXOF-UHFFFAOYSA-N N-hydroxy-2-methylpropanamine Chemical compound CC(C)CNO NDCGVLJXFQKXOF-UHFFFAOYSA-N 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 241000159610 Roya <green alga> Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QTENRWWVYAAPBI-YZTFXSNBSA-N Streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O QTENRWWVYAAPBI-YZTFXSNBSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000033289 adaptive immune response Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
- 201000004201 anogenital venereal wart Diseases 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- 230000007969 cellular immunity Effects 0.000 description 1
- 208000007951 cervical intraepithelial neoplasia Diseases 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000010611 checkerboard assay Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 229950001902 dimevamide Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- ABXBSVKCTZCZAG-UHFFFAOYSA-N ethyl 3-(5-methyltetrazol-1-yl)pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1N1C(C)=NN=N1 ABXBSVKCTZCZAG-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- VXAWCKIQYKXJMD-UHFFFAOYSA-N ethynamine Chemical compound NC#C VXAWCKIQYKXJMD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
- 208000008588 molluscum contagiosum Diseases 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 208000003154 papilloma Diseases 0.000 description 1
- 208000029211 papillomatosis Diseases 0.000 description 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- HUPQYPMULVBQDL-UHFFFAOYSA-N pentanoic acid Chemical compound CCCCC(O)=O.CCCCC(O)=O HUPQYPMULVBQDL-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- TWBYWOBDOCUKOW-ZQBYOMGUSA-N pyridine-4-carboxylic acid Chemical compound O[14C](=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-ZQBYOMGUSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000002943 spectrophotometric absorbance Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 239000012646 vaccine adjuvant Substances 0.000 description 1
- 229940124931 vaccine adjuvant Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/08—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis for Pneumocystis carinii
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Abstract
Имидазонафтиридин формулы (I) и тетрагидроимидазонафтиридин формулы (II) индуцируют биосинтез цитокинов, таких как интерферон и фактор некроза опухолей. Соединения проявляют антивирусную и антиопухолевую активность. Раскрыты также способы получения соединений и промежуточных соединений, полезных при получении вышеупомянутых соединений. Указанные R1 и R2, A и В определены в заявке.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6927697P | 1997-12-11 | 1997-12-11 | |
| PCT/US1998/026473 WO1999029693A1 (en) | 1997-12-11 | 1998-12-11 | Imidazonaphthyridines and their use in inducing cytokine biosynthesis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA67760C2 true UA67760C2 (ru) | 2004-07-15 |
Family
ID=22087889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000074070A UA67760C2 (ru) | 1997-12-11 | 1998-11-12 | Имидазонафтиридины и их применение для индуцирования биосинтеза цитокинов |
Country Status (28)
| Country | Link |
|---|---|
| US (14) | US6194425B1 (ru) |
| EP (1) | EP1040112B1 (ru) |
| JP (4) | JP4283438B2 (ru) |
| KR (3) | KR100642702B1 (ru) |
| CN (1) | CN1154647C (ru) |
| AT (3) | ATE277046T1 (ru) |
| AU (1) | AU753864B2 (ru) |
| BR (1) | BR9814275A (ru) |
| CA (1) | CA2311456C (ru) |
| CZ (1) | CZ307184B6 (ru) |
| DE (3) | DE69826518T2 (ru) |
| DK (1) | DK1512686T3 (ru) |
| EE (1) | EE04314B1 (ru) |
| ES (3) | ES2273138T3 (ru) |
| HK (1) | HK1070655A1 (ru) |
| HR (1) | HRP20000363B1 (ru) |
| HU (1) | HUP0101155A3 (ru) |
| IL (4) | IL136556A0 (ru) |
| NO (3) | NO316687B1 (ru) |
| NZ (1) | NZ504776A (ru) |
| PL (1) | PL193915B1 (ru) |
| PT (3) | PT1512685E (ru) |
| RU (3) | RU2312867C2 (ru) |
| SI (1) | SI1512686T1 (ru) |
| SK (2) | SK285872B6 (ru) |
| TR (1) | TR200001705T2 (ru) |
| UA (1) | UA67760C2 (ru) |
| WO (1) | WO1999029693A1 (ru) |
Families Citing this family (223)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| UA67760C2 (ru) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Имидазонафтиридины и их применение для индуцирования биосинтеза цитокинов |
| US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| CA2361936C (en) | 1999-01-08 | 2009-06-16 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating mucosal conditions |
| US6486168B1 (en) | 1999-01-08 | 2002-11-26 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| EP1438958A1 (en) * | 1999-06-10 | 2004-07-21 | 3M Innovative Properties Company | Carbamate substituted imidazoquinolines |
| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6541485B1 (en) * | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| SI1198233T1 (sl) * | 1999-06-10 | 2007-02-28 | 3M Innovative Properties Co | S sulfonamidom in sulfamidom substituirani imidazokinolini |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
| US6376669B1 (en) * | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
| US6894060B2 (en) | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20040209877A1 (en) * | 2000-04-13 | 2004-10-21 | Shelby Nancy J. | Methods for augmenting immune defenses contemplating the administration of phenolic and indoleamine-like compounds for use in animals ans humans |
| UA74593C2 (en) * | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| CA2430206A1 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| EP1850850A4 (en) * | 2000-12-08 | 2011-06-15 | 3M Innovative Properties Co | COMPOSITIONS AND METHOD FOR TARGETED ADMINISTRATION OF IMMUNE RESPONSE MODIFICATORS |
| US6664260B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6677347B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| UA74852C2 (en) | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| JP2005501550A (ja) * | 2001-08-30 | 2005-01-20 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調整剤分子を用いた形質細胞様樹状細胞を成熟させる方法 |
| DK1719511T3 (da) * | 2001-11-16 | 2009-04-14 | Coley Pharm Group Inc | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methansulfonamid, en farmaceutisk sammensætning omfattende samme, og anvendelse deraf |
| CA2467828C (en) * | 2001-11-29 | 2011-10-04 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| CA2365732A1 (en) * | 2001-12-20 | 2003-06-20 | Ibm Canada Limited-Ibm Canada Limitee | Testing measurements |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| BR0307788A (pt) * | 2002-02-22 | 2006-04-04 | 3M Innovative Properties Co | método de redução e tratamento de imunossupressão induzida por uv-b |
| WO2003103584A2 (en) | 2002-06-07 | 2003-12-18 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| NZ538812A (en) | 2002-08-15 | 2009-02-28 | 3M Innovative Properties Co | Immunostimulatory compositions and methods of stimulating an immune response |
| AU2003299082A1 (en) * | 2002-09-26 | 2004-04-19 | 3M Innovative Properties Company | 1h-imidazo dimers |
| WO2004053452A2 (en) * | 2002-12-11 | 2004-06-24 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| WO2004053057A2 (en) * | 2002-12-11 | 2004-06-24 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| MXPA05006740A (es) | 2002-12-20 | 2005-10-05 | 3M Innovative Properties Co | Imidazoquinolinas arilo-sustituidas. |
| US7387271B2 (en) | 2002-12-30 | 2008-06-17 | 3M Innovative Properties Company | Immunostimulatory combinations |
| EP1592302A4 (en) * | 2003-02-13 | 2007-04-25 | 3M Innovative Properties Co | METHODS AND COMPOSITIONS ASSOCIATED WITH IMMUNE RESPONSE MODIFIER COMPOUNDS AND TOLL-LIKE RECEPTOR 8 |
| WO2004075865A2 (en) * | 2003-02-27 | 2004-09-10 | 3M Innovative Properties Company | Selective modulation of tlr-mediated biological activity |
| JP2006519866A (ja) * | 2003-03-04 | 2006-08-31 | スリーエム イノベイティブ プロパティズ カンパニー | Ｕｖ誘発性の表皮の新形成の予防的治療 |
| US7163947B2 (en) * | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| TW200505458A (en) * | 2003-03-07 | 2005-02-16 | 3M Innovative Properties Co | 1-amino 1h-imidazoquinolines |
| WO2004080293A2 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods for diagnosing skin lesions |
| JP2006520245A (ja) | 2003-03-13 | 2006-09-07 | スリーエム イノベイティブ プロパティズ カンパニー | 入れ墨の除去方法 |
| EP1603510B1 (en) * | 2003-03-13 | 2012-05-09 | 3M Innovative Properties Company | Methods of improving skin quality |
| US20040192585A1 (en) | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| US7893096B2 (en) | 2003-03-28 | 2011-02-22 | Novartis Vaccines And Diagnostics, Inc. | Use of small molecule compounds for immunopotentiation |
| JP2007500210A (ja) * | 2003-04-10 | 2007-01-11 | スリーエム イノベイティブ プロパティズ カンパニー | 金属含有微粒子担体材料を使用した免疫反応調節物質化合物の送達 |
| US20040265351A1 (en) * | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| US20040214851A1 (en) * | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| US7731967B2 (en) | 2003-04-30 | 2010-06-08 | Novartis Vaccines And Diagnostics, Inc. | Compositions for inducing immune responses |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| WO2004110992A2 (en) * | 2003-06-06 | 2004-12-23 | 3M Innovative Properties Company | Process for imidazo[4,5-c] pyridin-4-amines |
| US6943255B2 (en) * | 2003-06-06 | 2005-09-13 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| MXPA06001004A (es) * | 2003-07-31 | 2006-04-27 | 3M Innovative Properties Co | Composiciones para encapsulacion y liberacion controlada. |
| CN1852711A (zh) * | 2003-08-05 | 2006-10-25 | 3M创新有限公司 | 使用免疫响应调节化合物的传染病预防 |
| WO2005018556A2 (en) * | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| PL1653959T3 (pl) * | 2003-08-14 | 2015-10-30 | 3M Innovative Properties Co | Modyfikatory odpowiedzi immunologicznej modyfikowane lipidami |
| ES2545826T3 (es) * | 2003-08-14 | 2015-09-16 | 3M Innovative Properties Company | Modificadores de la respuesta inmune modificados con lípidos |
| WO2005020912A2 (en) * | 2003-08-25 | 2005-03-10 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| AU2004266162A1 (en) * | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| EP1658076B1 (en) | 2003-08-27 | 2013-03-06 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| EP1663222A4 (en) * | 2003-09-02 | 2008-05-21 | 3M Innovative Properties Co | METHODS RELATING TO THE TREATMENT OF GIANCES |
| CA2537763A1 (en) * | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| WO2005033049A2 (en) * | 2003-10-01 | 2005-04-14 | Taro Pharmaceuticals U.S.A., Inc. | METHOD OF PREPARING 4-AMINO-1H-IMIDAZO(4,5-c)QUINOLINES AND ACID ADDITION SALTS THEREOF |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| AR046172A1 (es) | 2003-10-03 | 2005-11-30 | 3M Innovative Properties Co | Pirazolopiridinas y sus analogos; composiciones farmaceuticas que los contienen y su uso en la inhibicion de la biosintesis de citocinas |
| MXPA06003705A (es) | 2003-10-03 | 2006-06-20 | 3M Innovative Properties Co | Imidazoquinolinas sustituidas con alcoxi. |
| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| CA2543685A1 (en) * | 2003-10-31 | 2005-05-12 | 3M Innovative Properties Company | Neutrophil activation by immune response modifier compounds |
| CN1906193A (zh) * | 2003-11-14 | 2007-01-31 | 3M创新有限公司 | 肟取代的咪唑环化合物 |
| AU2004291122A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| EP1686992A4 (en) * | 2003-11-25 | 2009-11-04 | 3M Innovative Properties Co | HYDROXYLAMINE, AND IMIDAZOQUINOLEINS, AND IMIDAZOPYRIDINES AND IMIDAZONAPHTYRIDINE SUBSTITUTED WITH OXIME |
| MY161812A (en) | 2003-11-25 | 2017-05-15 | 3M Innovative Properties Co | Substituted imidazo ring systems and methods |
| US20050226878A1 (en) * | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| WO2005055932A2 (en) * | 2003-12-02 | 2005-06-23 | 3M Innovative Properties Company | Therapeutic combinations and methods including irm compounds |
| TW200533352A (en) * | 2003-12-04 | 2005-10-16 | 3M Innovative Properties Co | Sulfone substituted imidazo ring ethers |
| US8802853B2 (en) * | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| CA2552101A1 (en) * | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds |
| WO2005066169A2 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| EP1699398A4 (en) * | 2003-12-30 | 2007-10-17 | 3M Innovative Properties Co | IMPROVING THE IMMUNE RESPONSE |
| ES2665342T3 (es) * | 2004-03-15 | 2018-04-25 | Meda Ab | Formulaciones y métodos para modificadores de la respuesta inmune |
| TW200612932A (en) | 2004-03-24 | 2006-05-01 | 3M Innovative Properties Co | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| EP1735010A4 (en) * | 2004-04-09 | 2008-08-27 | 3M Innovative Properties Co | METHODS, COMPOSITIONS AND PREPARATIONS FOR ADMINISTRATION OF IMMUNE RESPONSE MODIFIERS (MRI) |
| WO2006126981A2 (en) * | 2004-04-28 | 2006-11-30 | 3M Innovative Properties Company | Compositions and methods for mucosal vaccination |
| US20050267145A1 (en) * | 2004-05-28 | 2005-12-01 | Merrill Bryon A | Treatment for lung cancer |
| WO2005123079A2 (en) * | 2004-06-14 | 2005-12-29 | 3M Innovative Properties Company | Urea substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US8026366B2 (en) * | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006009832A1 (en) * | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| US7897609B2 (en) * | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US7915281B2 (en) * | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| WO2006028545A2 (en) * | 2004-06-18 | 2006-03-16 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US8541438B2 (en) * | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US20110104186A1 (en) | 2004-06-24 | 2011-05-05 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
| WO2006002422A2 (en) | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | Compounds for immunopotentiation |
| EP1786450A4 (en) * | 2004-08-27 | 2009-11-11 | 3M Innovative Properties Co | HIV IMMUNOSTIMATORY COMPOSITIONS |
| US8143270B2 (en) | 2004-09-02 | 2012-03-27 | 3M Innovative Properties Company | 2-amino 1H-in-imidazo ring systems and methods |
| WO2006026760A2 (en) * | 2004-09-02 | 2006-03-09 | 3M Innovative Properties Company | 1-amino imidazo-containing compounds and methods |
| AU2005282726B2 (en) * | 2004-09-02 | 2011-06-02 | 3M Innovative Properties Company | 1-alkoxy 1H-imidazo ring systems and methods |
| WO2006029223A2 (en) * | 2004-09-08 | 2006-03-16 | Children's Medical Center Corporation | Method for stimulating the immune response of newborns |
| US20070243215A1 (en) * | 2004-10-08 | 2007-10-18 | Miller Richard L | Adjuvant for Dna Vaccines |
| US7557211B2 (en) * | 2004-11-12 | 2009-07-07 | Bristol-Myers Squibb Company | 8H-imidazo[4,5-D]thiazolo[4,5-B]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| ES2377758T3 (es) | 2004-11-12 | 2012-03-30 | Bristol-Myers Squibb Company | Compuestos tricíclicos basados en tiazolo[4,5-b]piridina imidazo-fusionada y composiciones farmacéuticas que los comprenden |
| EP1819364A4 (en) * | 2004-12-08 | 2010-12-29 | 3M Innovative Properties Co | COMPOSITIONS, IMMUNOMODULATORY COMBINATIONS AND ASSOCIATED METHODS |
| US8080560B2 (en) * | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| AU2005323023A1 (en) * | 2004-12-30 | 2006-07-13 | Takeda Pharmaceutical Company Limited | 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine ethanesulfonate and 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine methanesulfonate |
| WO2006083440A2 (en) | 2004-12-30 | 2006-08-10 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| EP1830876B1 (en) | 2004-12-30 | 2015-04-08 | Meda AB | Use of imiquimod for the treatment of cutaneous metastases derived from a breast cancer tumor |
| US8436176B2 (en) * | 2004-12-30 | 2013-05-07 | Medicis Pharmaceutical Corporation | Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine |
| JP5543068B2 (ja) | 2004-12-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| CN101146800A (zh) | 2005-01-27 | 2008-03-19 | 生物工程大学精神物质实验室 | 用于治疗阿尔茨海默病的有机化合物，它们的用途和制备方法 |
| CA2597092A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| JP5122980B2 (ja) * | 2005-02-09 | 2013-01-16 | スリーエム イノベイティブ プロパティズ カンパニー | アルキルオキシ置換チアゾロキノリン類およびアルキルオキシ置換チアゾロナフチリデン類 |
| US8378102B2 (en) | 2005-02-09 | 2013-02-19 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted thiazolo[4,5-c] ring compounds and methods |
| CA2597446A1 (en) * | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| WO2006086634A2 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| CA2598695A1 (en) * | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| EP1851220A2 (en) * | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| US8158794B2 (en) * | 2005-02-23 | 2012-04-17 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| WO2006091647A2 (en) * | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| AU2006223148A1 (en) * | 2005-03-14 | 2006-09-21 | 3M Innovative Properties Company | Method of treating actinic keratosis |
| AU2006232377A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| EP1863770A4 (en) * | 2005-04-01 | 2010-05-05 | Coley Pharm Group Inc | RING CLOSURE AND CORRESPONDING METHODS AND INTERMEDIATE PRODUCTS |
| CA2602590A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| AU2006241166A1 (en) * | 2005-04-25 | 2006-11-02 | 3M Innovative Properties Company | Immunostimulatory compositions |
| JP2009507795A (ja) * | 2005-08-31 | 2009-02-26 | スミスクライン ビーチャム コーポレーション | 化合物 |
| ZA200803029B (en) * | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| US8476292B2 (en) * | 2005-09-09 | 2013-07-02 | 3M Innovative Properties Company | Amide and carbamate derivatives of N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c] quinolin-1-Yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| US8889154B2 (en) | 2005-09-15 | 2014-11-18 | Medicis Pharmaceutical Corporation | Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation |
| US8088790B2 (en) | 2005-11-04 | 2012-01-03 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazoquinolines and methods |
| WO2007079086A1 (en) * | 2005-12-28 | 2007-07-12 | Coley Pharmaceutical Group, Inc. | Pyrazoloalkyl substituted imidazo ring compounds and methods |
| EP3085373A1 (en) | 2006-02-22 | 2016-10-26 | 3M Innovative Properties Company | Immune response modifier conjugates |
| US8088788B2 (en) | 2006-03-15 | 2012-01-03 | 3M Innovative Properties Company | Substituted fused[1,2] imidazo[4,5-c] ring compounds and methods |
| WO2007106854A2 (en) * | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods |
| ES2536426T3 (es) | 2006-03-23 | 2015-05-25 | Novartis Ag | Compuestos de imidazoquinoxalina como inmunomoduladores |
| WO2007143526A2 (en) * | 2006-06-05 | 2007-12-13 | Coley Pharmaceutical Group, Inc. | Substituted tetrahydroimidazonaphthyridines and methods |
| WO2008008432A2 (en) * | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| AU2007275815A1 (en) * | 2006-07-18 | 2008-01-24 | Wirra Ip Pty. Ltd. | Immune response modifier formulations |
| CA2659733A1 (en) * | 2006-07-31 | 2008-02-07 | 3M Innovative Properties Company | Sterilized topical compositions of 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine |
| US8178539B2 (en) * | 2006-09-06 | 2012-05-15 | 3M Innovative Properties Company | Substituted 3,4,6,7-tetrahydro-5H-1,2a,4a,8-tetraazacyclopenta[cd]phenalenes and methods |
| US20080149123A1 (en) * | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| CN101568351B (zh) * | 2006-12-22 | 2012-05-30 | 3M创新有限公司 | 控制释放的组合物和方法 |
| WO2008098232A1 (en) * | 2007-02-08 | 2008-08-14 | Graceway Pharmaceuticals, Llc | Methods of treating dermatological disorders and inducing interferon biosynthesis with shorter durations of imiquimod therapy |
| US20100160368A1 (en) | 2008-08-18 | 2010-06-24 | Gregory Jefferson J | Methods of Treating Dermatological Disorders and Inducing Interferon Biosynthesis With Shorter Durations of Imiquimod Therapy |
| RS58566B1 (sr) | 2008-12-19 | 2019-05-31 | Medicis Pharmaceutical Corp | Formulacije imikuimoda niže dozne jačine i kratkih režima doziranja za lečenje aktinične keratoze |
| AU2010229835B2 (en) | 2009-03-25 | 2015-01-15 | The Board Of Regents Of The University Of Texas System | Compositions for stimulation of mammalian innate immune resistance to pathogens |
| AU2010232731A1 (en) * | 2009-03-31 | 2011-10-20 | Arqule, Inc. | Substituted dipyrido-pyrimido-diazepine and benzo-pyrido-pyrimido compounds |
| US8511006B2 (en) * | 2009-07-02 | 2013-08-20 | Owens Corning Intellectual Capital, Llc | Building-integrated solar-panel roof element systems |
| GEP20156418B (en) | 2009-07-13 | 2016-01-11 | Medicis Pharmaceutical Corp | Lower dosage strength imiquimod formulations and short dosing regimens for treating genital and perianal warts |
| US20110033515A1 (en) * | 2009-08-04 | 2011-02-10 | Rst Implanted Cell Technology | Tissue contacting material |
| US8461328B2 (en) * | 2010-01-12 | 2013-06-11 | Genentech, Inc. | Tricyclic heterocyclic compounds, compositions and methods of use thereof |
| DK2584900T3 (en) | 2010-06-25 | 2019-04-01 | Medicis Pharmaceutical Corp | Combination therapy with cryosurgery and low-dose imiquimod for the treatment of actinic keratosis |
| EP2606047B1 (en) | 2010-08-17 | 2017-01-25 | 3M Innovative Properties Company | Lipidated immune response modifier compound compositions, formulations, and methods |
| US9475804B2 (en) | 2011-06-03 | 2016-10-25 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| AU2012261959B2 (en) | 2011-06-03 | 2015-12-03 | Solventum Intellectual Properties Company | Hydrazino 1H-imidazoquinolin-4-amines and conjugates made therefrom |
| US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
| US9492682B2 (en) | 2011-09-14 | 2016-11-15 | Medicis Pharmaceutical Corporation | Combination therapy with low dosage strength imiquimod and photodynamic therapy to treat actinic keratosis |
| CA2857664A1 (en) | 2011-11-30 | 2013-06-06 | Sarepta Therapeutics, Inc. | Antisense oligonucleotides targeting within the smn2 pre-mrna for use ininduced exon inclusion in spinal muscle atrophy |
| CA2871490C (en) | 2012-04-27 | 2022-10-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Use of cpg oligonucleotides co-formulated with an antibiotic to accelerate wound healing |
| WO2013164754A2 (en) | 2012-05-04 | 2013-11-07 | Pfizer Inc. | Prostate-associated antigens and vaccine-based immunotherapy regimens |
| CN112587658A (zh) | 2012-07-18 | 2021-04-02 | 博笛生物科技有限公司 | 癌症的靶向免疫治疗 |
| CN105025854A (zh) | 2013-01-07 | 2015-11-04 | 宾夕法尼亚大学董事会 | 治疗皮肤t细胞淋巴瘤的组合物和方法 |
| WO2015011254A1 (en) | 2013-07-26 | 2015-01-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of bacterial infections |
| KR102258645B1 (ko) | 2013-11-05 | 2021-05-28 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 참기름을 베이스로 하는 주사 제제 |
| WO2015092592A1 (en) | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| AU2015205753A1 (en) | 2014-01-10 | 2016-07-21 | Birdie Biopharmaceuticals Inc. | Compounds and compositions for treating HER2 positive tumors |
| DK3166976T3 (da) | 2014-07-09 | 2022-04-11 | Birdie Biopharmaceuticals Inc | Anti-pd-l1-kombinationer til behandling af tumorer |
| CN112546230A (zh) | 2014-07-09 | 2021-03-26 | 博笛生物科技有限公司 | 用于治疗癌症的联合治疗组合物和联合治疗方法 |
| CN112546238A (zh) | 2014-09-01 | 2021-03-26 | 博笛生物科技有限公司 | 用于治疗肿瘤的抗-pd-l1结合物 |
| WO2016180852A1 (en) | 2015-05-12 | 2016-11-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preparing antigen-specific t cells from an umbilical cord blood sample |
| EP3298131B1 (en) | 2015-05-20 | 2023-04-26 | The Regents of The University of California | Method for generating human dendritic cells for immunotherapy |
| US10150768B2 (en) | 2015-08-31 | 2018-12-11 | 3M Innovative Properties Company | Guanidine substituted imidazo[4,5-c] ring compounds |
| CN107922416B (zh) | 2015-08-31 | 2021-07-02 | 3M创新有限公司 | 含有取代的胍基团的咪唑并[4,5-c]环化合物 |
| CN108137586B (zh) * | 2015-09-14 | 2021-04-13 | 辉瑞大药厂 | 作为LRRK2抑制剂的新颖咪唑并[4,5-c]喹啉和咪唑并[4,5-c][1,5]萘啶衍生物 |
| US10526309B2 (en) | 2015-10-02 | 2020-01-07 | The University Of North Carolina At Chapel Hill | Pan-TAM inhibitors and Mer/Axl dual inhibitors |
| CN115252792A (zh) | 2016-01-07 | 2022-11-01 | 博笛生物科技有限公司 | 用于治疗肿瘤的抗-egfr组合 |
| CN115554406A (zh) | 2016-01-07 | 2023-01-03 | 博笛生物科技有限公司 | 用于治疗肿瘤的抗-cd20组合 |
| CN106943598A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-her2组合 |
| JP6883806B2 (ja) * | 2016-03-09 | 2021-06-09 | 国立大学法人大阪大学 | 化合物、及びこれを含む有機半導体材料 |
| BR112018073676B1 (pt) | 2016-05-16 | 2023-10-03 | University Of Virginia Patent Foundation | Lipossomas peguilados e métodos de uso |
| EP3458475B1 (en) | 2016-05-16 | 2022-07-27 | Access to Advanced Health Institute | Formulation containing tlr agonist and methods of use |
| EP3504215B1 (en) | 2016-08-26 | 2022-04-06 | 3M Innovative Properties Company | Fused [1,2]imidazo[4,5-c]ring compounds substituted with guanidino groups |
| CA3033542A1 (en) | 2016-08-30 | 2018-03-08 | Dana-Farber Cancer Institute, Inc. | Compositions and uses of biomaterials and activators of innate immunity |
| MX2019005502A (es) | 2016-11-09 | 2020-10-01 | Univ Texas | Metodos y composiciones para inmunomodulacion adaptativa. |
| CA3045666A1 (en) | 2016-12-14 | 2018-06-21 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a jak inhibitor and devices |
| US11426566B2 (en) | 2016-12-14 | 2022-08-30 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with a TLR modulator |
| AU2017378406A1 (en) | 2016-12-14 | 2019-06-13 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with an immunosuppressant |
| EP3554345A1 (en) | 2016-12-14 | 2019-10-23 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a smad7 inhibitor |
| EP3554541B1 (en) | 2016-12-14 | 2023-06-07 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with a chemokine/chemokine receptor inhibitor |
| CN110072551B (zh) | 2016-12-14 | 2023-05-23 | 比奥拉治疗股份有限公司 | 使用利用可摄入装置释放的il-12/il-23抑制剂治疗胃肠道疾病 |
| WO2018160552A1 (en) | 2017-03-01 | 2018-09-07 | 3M Innovative Properties Company | IMIDAZO[4,5-c] RING COMPOUNDS CONTAINING GUANIDINE SUBSTITUTED BENZAMIDE GROUPS |
| US11596670B2 (en) | 2017-03-30 | 2023-03-07 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with IL-10 or an IL-10 agonist |
| CN108794467A (zh) | 2017-04-27 | 2018-11-13 | 博笛生物科技有限公司 | 2-氨基-喹啉衍生物 |
| AR111760A1 (es) | 2017-05-19 | 2019-08-14 | Novartis Ag | Compuestos y composiciones para el tratamiento de tumores sólidos mediante administración intratumoral |
| EP3641771A4 (en) | 2017-06-23 | 2020-12-16 | Birdie Biopharmaceuticals, Inc. | PHARMACEUTICAL COMPOSITIONS |
| ES2951817T3 (es) | 2017-08-22 | 2023-10-25 | Dynavax Tech Corp | Derivados de imidazoquinolina de cadena alquílica modificada como agonistas de TLR7/8 y usos de los mismos |
| US10722591B2 (en) | 2017-11-14 | 2020-07-28 | Dynavax Technologies Corporation | Cleavable conjugates of TLR7/8 agonist compounds, methods for preparation, and uses thereof |
| JP7197244B2 (ja) | 2017-12-20 | 2022-12-27 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤として使用するための分岐鎖連結基を有するアミド置換イミダゾ［４，５－ｃ］キノリン化合物 |
| JP7251893B2 (ja) | 2018-02-28 | 2023-04-04 | スリーエム イノベイティブ プロパティズ カンパニー | Ｎ－１分枝基を有する置換イミダゾ［４，５－ｃ］キノリン化合物 |
| KR20200128116A (ko) | 2018-02-28 | 2020-11-11 | 화이자 인코포레이티드 | Il-15 변이체 및 이의 용도 |
| MX2020012607A (es) | 2018-05-23 | 2021-01-29 | Pfizer | Anticuerpos especificos para gucy2c y sus usos. |
| MX2020012539A (es) | 2018-05-23 | 2021-02-16 | Pfizer | Anticuerpos especificos para cd3 y sus usos. |
| CN112218864B (zh) | 2018-05-24 | 2023-09-08 | 3M创新有限公司 | N-1支链环烷基取代的咪唑并[4,5-c]喹啉化合物、组合物和方法 |
| EP3887369A1 (en) | 2018-11-26 | 2021-10-06 | 3M Innovative Properties Company | N-1 branched alkyl ether substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| WO2020128893A1 (en) | 2018-12-21 | 2020-06-25 | Pfizer Inc. | Combination treatments of cancer comprising a tlr agonist |
| WO2020245706A1 (en) | 2019-06-06 | 2020-12-10 | 3M Innovative Properties Company | N-1 branched alkyl substituted imidazo[4,5-c]quinoline compounds, compositions, and methods |
| CN113906027A (zh) | 2019-06-12 | 2022-01-07 | 3M创新有限公司 | 具有N-1支链基团的苯乙基取代的咪唑并[4,5-c]喹啉化合物 |
| WO2021116420A1 (en) | 2019-12-13 | 2021-06-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of tlr7 and/or tlr8 agonists for the treatment of leptospirosis |
| JP7369297B2 (ja) | 2019-12-17 | 2023-10-25 | ファイザー・インク | Ｃｄ４７、ｐｄ－ｌ１に特異的な抗体、およびその使用 |
| WO2022009157A1 (en) | 2020-07-10 | 2022-01-13 | Novartis Ag | Lhc165 and spartalizumab combinations for treating solid tumors |
| EP4182346A1 (en) | 2020-07-17 | 2023-05-24 | Pfizer Inc. | Therapeutic antibodies and their uses |
Family Cites Families (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314941A (en) | 1964-06-23 | 1967-04-18 | American Cyanamid Co | Novel substituted pyridodiazepins |
| US3764681A (en) * | 1970-07-08 | 1973-10-09 | Lilly Co Eli | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents |
| US3917624A (en) | 1972-09-27 | 1975-11-04 | Pfizer | Process for producing 2-amino-nicotinonitrile intermediates |
| ZA848968B (en) | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| US5238944A (en) | 1988-12-15 | 1993-08-24 | Riker Laboratories, Inc. | Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine |
| US5756747A (en) | 1989-02-27 | 1998-05-26 | Riker Laboratories, Inc. | 1H-imidazo 4,5-c!quinolin-4-amines |
| US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| US5037986A (en) | 1989-03-23 | 1991-08-06 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo[4,5-c]quinolin-4-amines |
| NZ232740A (en) | 1989-04-20 | 1992-06-25 | Riker Laboratories Inc | Solution for parenteral administration comprising a 1h-imidazo(4,5-c) quinolin-4-amine derivative, an acid and a tonicity adjuster |
| US4988815A (en) | 1989-10-26 | 1991-01-29 | Riker Laboratories, Inc. | 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines |
| EP0553202B1 (en) | 1990-10-05 | 1995-04-12 | Minnesota Mining And Manufacturing Company | Process for the preparation of imidazo[4,5-c]quinolin-4-amines |
| US5389640A (en) | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5175296A (en) | 1991-03-01 | 1992-12-29 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| US5268376A (en) | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5378698A (en) * | 1991-10-21 | 1995-01-03 | Shionogi & Co., Ltd. | Benzothiazepine derivatives |
| US5266575A (en) | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-4-amines |
| IL105325A (en) | 1992-04-16 | 1996-11-14 | Minnesota Mining & Mfg | Immunogen/vaccine adjuvant composition |
| US5395937A (en) | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| US5352784A (en) | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5648516A (en) | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| KR100341341B1 (ko) | 1993-07-15 | 2002-11-25 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | 이미다조[4,5-c]피리딘-4-아민 |
| US5644063A (en) | 1994-09-08 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]pyridin-4-amine intermediates |
| US5482936A (en) | 1995-01-12 | 1996-01-09 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-C]quinoline amines |
| US5585612A (en) | 1995-03-20 | 1996-12-17 | Harp Enterprises, Inc. | Method and apparatus for voting |
| JPH09208584A (ja) | 1996-01-29 | 1997-08-12 | Terumo Corp | アミド誘導体、およびそれを含有する医薬製剤、および合成中間体 |
| JPH09255926A (ja) | 1996-03-26 | 1997-09-30 | Diatex Co Ltd | 粘着テープ |
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| US5693811A (en) | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| ATE367159T1 (de) | 1996-10-25 | 2007-08-15 | Minnesota Mining & Mfg | Verbindungen, die die immunantwort verändern, zur behandlung von th2-vermittelten und -verwandten krankheiten |
| PT839810E (pt) * | 1996-11-04 | 2003-01-31 | Bayer Cropscience Sa | 1-poliarilpirazois como pesticidas |
| US5939090A (en) | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| EP0894797A4 (en) | 1997-01-09 | 2001-08-16 | Terumo Corp | NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS |
| UA67760C2 (ru) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Имидазонафтиридины и их применение для индуцирования биосинтеза цитокинов |
| JPH11222432A (ja) | 1998-02-03 | 1999-08-17 | Terumo Corp | インターフェロンを誘起するアミド誘導体を含有する外用剤 |
| JPH11255926A (ja) | 1998-03-13 | 1999-09-21 | Toray Ind Inc | シリコーン成型品およびその製造方法 |
| US6110929A (en) | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| JP2000119271A (ja) * | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| US6518280B2 (en) * | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| CA2361936C (en) | 1999-01-08 | 2009-06-16 | 3M Innovative Properties Company | Formulations comprising imiquimod or other immune response modifiers for treating mucosal conditions |
| US6545485B1 (en) * | 1999-01-21 | 2003-04-08 | Radar Engineers | Ultrasonic pinpointer for power system sources of interference |
| US6558951B1 (en) | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| JP2000247884A (ja) | 1999-03-01 | 2000-09-12 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6573273B1 (en) * | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6331539B1 (en) | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6660260B1 (en) * | 1999-09-21 | 2003-12-09 | Mayo Foundation For Medical Education And Research | Bioprosthetic heart valves |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| US6894060B2 (en) * | 2000-03-30 | 2005-05-17 | 3M Innovative Properties Company | Method for the treatment of dermal lesions caused by envenomation |
| US20020055517A1 (en) | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| JP2002145777A (ja) | 2000-11-06 | 2002-05-22 | Sumitomo Pharmaceut Co Ltd | アラキドン酸誘発皮膚疾患治療剤 |
| UA74852C2 (en) | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
| UA74593C2 (en) | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6664265B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| CA2430206A1 (en) * | 2000-12-08 | 2002-06-13 | 3M Innovative Properties Company | Screening method for identifying compounds that selectively induce interferon alpha |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6677348B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6664260B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Heterocyclic ether substituted imidazoquinolines |
| CN1523987A (zh) | 2001-06-15 | 2004-08-25 | 3M创新有限公司 | 治疗牙周疾病的免疫反应调节剂 |
| JP2005501550A (ja) | 2001-08-30 | 2005-01-20 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調整剤分子を用いた形質細胞様樹状細胞を成熟させる方法 |
| US6667347B2 (en) * | 2001-09-14 | 2003-12-23 | Chevron U.S.A. Inc. | Scrubbing CO2 from methane-containing gases using an aqueous stream |
| AU2002360278A1 (en) * | 2001-10-12 | 2003-11-11 | Coley Pharmaceutical Gmbh | Methods and products for enhancing immune responses using imidazoquinoline compounds |
| DK1719511T3 (da) * | 2001-11-16 | 2009-04-14 | Coley Pharm Group Inc | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methansulfonamid, en farmaceutisk sammensætning omfattende samme, og anvendelse deraf |
| CA2467828C (en) * | 2001-11-29 | 2011-10-04 | 3M Innovative Properties Company | Pharmaceutical formulations comprising an immune response modifier |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| BR0307788A (pt) * | 2002-02-22 | 2006-04-04 | 3M Innovative Properties Co | método de redução e tratamento de imunossupressão induzida por uv-b |
| GB0211649D0 (en) | 2002-05-21 | 2002-07-03 | Novartis Ag | Organic compounds |
| JP2005531599A (ja) * | 2002-05-29 | 2005-10-20 | スリーエム イノベイティブ プロパティズ カンパニー | イミダゾ［４，５−ｃ］ピリジン−４−アミンのための方法 |
| WO2003103584A2 (en) * | 2002-06-07 | 2003-12-18 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| NZ538812A (en) * | 2002-08-15 | 2009-02-28 | 3M Innovative Properties Co | Immunostimulatory compositions and methods of stimulating an immune response |
| AU2003299082A1 (en) * | 2002-09-26 | 2004-04-19 | 3M Innovative Properties Company | 1h-imidazo dimers |
| AU2003290988A1 (en) * | 2002-11-14 | 2004-06-15 | Pintex Pharmaceuticals, Inc. | Levels of pin1 in normal and cancerous tissue |
| WO2004053452A2 (en) * | 2002-12-11 | 2004-06-24 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| WO2004053057A2 (en) * | 2002-12-11 | 2004-06-24 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| MXPA05006740A (es) * | 2002-12-20 | 2005-10-05 | 3M Innovative Properties Co | Imidazoquinolinas arilo-sustituidas. |
| US7387271B2 (en) * | 2002-12-30 | 2008-06-17 | 3M Innovative Properties Company | Immunostimulatory combinations |
| EP1592302A4 (en) * | 2003-02-13 | 2007-04-25 | 3M Innovative Properties Co | METHODS AND COMPOSITIONS ASSOCIATED WITH IMMUNE RESPONSE MODIFIER COMPOUNDS AND TOLL-LIKE RECEPTOR 8 |
| WO2004075865A2 (en) * | 2003-02-27 | 2004-09-10 | 3M Innovative Properties Company | Selective modulation of tlr-mediated biological activity |
| JP2006519866A (ja) * | 2003-03-04 | 2006-08-31 | スリーエム イノベイティブ プロパティズ カンパニー | Ｕｖ誘発性の表皮の新形成の予防的治療 |
| TW200505458A (en) * | 2003-03-07 | 2005-02-16 | 3M Innovative Properties Co | 1-amino 1h-imidazoquinolines |
| WO2004080293A2 (en) * | 2003-03-13 | 2004-09-23 | 3M Innovative Properties Company | Methods for diagnosing skin lesions |
| JP2006520245A (ja) * | 2003-03-13 | 2006-09-07 | スリーエム イノベイティブ プロパティズ カンパニー | 入れ墨の除去方法 |
| EP1603510B1 (en) * | 2003-03-13 | 2012-05-09 | 3M Innovative Properties Company | Methods of improving skin quality |
| EP1613956A2 (en) * | 2003-03-25 | 2006-01-11 | 3M Innovative Properties Company | Selective activation of cellular activities mediated through a common toll-like receptor |
| US20040192585A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| JP2007500210A (ja) * | 2003-04-10 | 2007-01-11 | スリーエム イノベイティブ プロパティズ カンパニー | 金属含有微粒子担体材料を使用した免疫反応調節物質化合物の送達 |
| US20040214851A1 (en) * | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| GEP20084545B (en) * | 2003-09-05 | 2008-11-25 | Anadys Pharmaceuticals Inc | Introducing tlr7 ligands and prodrugs thereof for the treatment of hepatitis c viral infection |
| AU2005323023A1 (en) * | 2004-12-30 | 2006-07-13 | Takeda Pharmaceutical Company Limited | 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine ethanesulfonate and 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine methanesulfonate |
-
1998
- 1998-11-12 UA UA2000074070A patent/UA67760C2/ru unknown
- 1998-12-11 EE EEP200000349A patent/EE04314B1/xx not_active IP Right Cessation
- 1998-12-11 DE DE69826518T patent/DE69826518T2/de not_active Expired - Fee Related
- 1998-12-11 US US09/210,114 patent/US6194425B1/en not_active Expired - Fee Related
- 1998-12-11 PL PL98341159A patent/PL193915B1/pl not_active IP Right Cessation
- 1998-12-11 HU HU0101155A patent/HUP0101155A3/hu unknown
- 1998-12-11 PT PT04022440T patent/PT1512685E/pt unknown
- 1998-12-11 CN CNB988135639A patent/CN1154647C/zh not_active Expired - Fee Related
- 1998-12-11 SK SK835-2000A patent/SK285872B6/sk not_active IP Right Cessation
- 1998-12-11 ES ES04022441T patent/ES2273138T3/es not_active Expired - Lifetime
- 1998-12-11 ES ES04022440T patent/ES2270249T3/es not_active Expired - Lifetime
- 1998-12-11 WO PCT/US1998/026473 patent/WO1999029693A1/en active Application Filing
- 1998-12-11 JP JP2000524286A patent/JP4283438B2/ja not_active Expired - Fee Related
- 1998-12-11 EP EP98963888A patent/EP1040112B1/en not_active Expired - Lifetime
- 1998-12-11 SK SK5035-2007A patent/SK286304B6/sk not_active IP Right Cessation
- 1998-12-11 AT AT98963888T patent/ATE277046T1/de not_active IP Right Cessation
- 1998-12-11 DE DE69835309T patent/DE69835309T2/de not_active Expired - Lifetime
- 1998-12-11 PT PT04022441T patent/PT1512686E/pt unknown
- 1998-12-11 AT AT04022441T patent/ATE338757T1/de not_active IP Right Cessation
- 1998-12-11 RU RU2003126259/04A patent/RU2312867C2/ru not_active IP Right Cessation
- 1998-12-11 KR KR1020037016102A patent/KR100642702B1/ko not_active IP Right Cessation
- 1998-12-11 KR KR1020037016103A patent/KR100563175B1/ko not_active IP Right Cessation
- 1998-12-11 ES ES98963888T patent/ES2227902T3/es not_active Expired - Lifetime
- 1998-12-11 NZ NZ504776A patent/NZ504776A/en unknown
- 1998-12-11 TR TR2000/01705T patent/TR200001705T2/xx unknown
- 1998-12-11 KR KR1020007006369A patent/KR100642703B1/ko not_active IP Right Cessation
- 1998-12-11 AT AT04022440T patent/ATE333456T1/de active
- 1998-12-11 SI SI9830868T patent/SI1512686T1/sl unknown
- 1998-12-11 RU RU2000114496/04A patent/RU2221798C2/ru active
- 1998-12-11 DE DE69835844T patent/DE69835844T2/de not_active Expired - Fee Related
- 1998-12-11 RU RU2003126258/04A patent/RU2314307C2/ru active
- 1998-12-11 AU AU19123/99A patent/AU753864B2/en not_active Ceased
- 1998-12-11 CA CA2311456A patent/CA2311456C/en not_active Expired - Lifetime
- 1998-12-11 DK DK04022441T patent/DK1512686T3/da active
- 1998-12-11 PT PT98963888T patent/PT1040112E/pt unknown
- 1998-12-11 CZ CZ2007-268A patent/CZ307184B6/cs not_active IP Right Cessation
- 1998-12-11 BR BR9814275-5A patent/BR9814275A/pt not_active IP Right Cessation
- 1998-12-11 IL IL13655698A patent/IL136556A0/xx active IP Right Grant
-
2000
- 2000-05-24 NO NO20002663A patent/NO316687B1/no not_active IP Right Cessation
- 2000-06-02 HR HR20000363A patent/HRP20000363B1/xx not_active IP Right Cessation
- 2000-06-05 IL IL136556A patent/IL136556A/en not_active IP Right Cessation
- 2000-11-06 US US09/706,990 patent/US6514985B1/en not_active Expired - Fee Related
-
2001
- 2001-08-31 US US09/945,197 patent/US6624172B2/en not_active Expired - Lifetime
-
2002
- 2002-06-27 US US10/185,387 patent/US6693113B2/en not_active Expired - Lifetime
- 2002-06-27 US US10/184,304 patent/US6638944B2/en not_active Expired - Fee Related
- 2002-10-07 US US10/265,956 patent/US6699878B2/en not_active Expired - Fee Related
-
2003
- 2003-04-02 US US10/405,321 patent/US6747040B2/en not_active Expired - Fee Related
- 2003-04-03 US US10/406,181 patent/US6797716B2/en not_active Expired - Lifetime
- 2003-12-19 NO NO20035719A patent/NO20035719D0/no unknown
- 2003-12-19 NO NO20035718A patent/NO328045B1/no not_active IP Right Cessation
-
2004
- 2004-04-14 US US10/824,232 patent/US6894165B2/en not_active Expired - Fee Related
- 2004-12-03 US US11/004,674 patent/US6949646B2/en not_active Expired - Lifetime
-
2005
- 2005-04-21 HK HK05103436A patent/HK1070655A1/xx not_active IP Right Cessation
- 2005-07-25 US US11/188,418 patent/US7038051B2/en not_active Expired - Lifetime
- 2005-12-12 JP JP2005358302A patent/JP4203067B2/ja not_active Expired - Fee Related
-
2006
- 2006-02-13 US US11/276,074 patent/US7335773B2/en not_active Expired - Fee Related
- 2006-09-14 IL IL178092A patent/IL178092A/en not_active IP Right Cessation
- 2006-09-14 IL IL178091A patent/IL178091A/en not_active IP Right Cessation
-
2007
- 2007-03-28 US US11/692,701 patent/US20070167481A1/en not_active Abandoned
- 2007-07-11 JP JP2007181872A patent/JP2007262093A/ja not_active Withdrawn
- 2007-12-06 US US11/999,602 patent/US7678918B2/en not_active Expired - Fee Related
- 2007-12-26 JP JP2007335120A patent/JP2008115190A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA67760C2 (ru) | Имидазонафтиридины и их применение для индуцирования биосинтеза цитокинов | |
| KR101130928B1 (ko) | 치환된 이미다조 고리 시스템 및 방법 | |
| US6518280B2 (en) | Imidazonaphthyridines | |
| WO2006091568A2 (en) | Hydroxyalkyl substituted imidazonaphthyridines | |
| CZ303462B6 (cs) | Imidazo[4,5-c]chinolinový nebo 6,7,8,9-tetrahydroimidazo[4,5-c]chinolinový derivát a farmaceutická kompozice s jeho obsahem | |
| UA73503C2 (ru) | Замещенные сульфонамидом и сульфамидом имидазохинолины | |
| EP1512685A1 (en) | Imidazonaphthyridines and their use in inducing cytokine biosythesis | |
| CZ20002158A3 (cs) | Imidazonaftyridiny a jejich použití při indukci biosyntézy cytokinu | |
| MXPA00005684A (es) | Imidazonaftiridinas y su uso en la induccion de biosintesis de citocina |